There's no doubt that Keanu Reeves [1] really is one of Hollywood's most notable "good guys." [2] To some, that reputation might make it somewhat surprising that Reeves is, at the age of 55, single and never married (at least not intentionally [3]!). Although Reeves has been publicly single for many years, it seems like he may be off the market. The actor sparked romance rumors when he held hands with his longtime friend, artist Alexandra Grant, at the LACMA Art + Film Gala in LA on Saturday.
Reeves's past relationships have mostly been with other actors, some famous, some not famous at all. If you're curious about the ageless star [4]'s past romances, we've got you covered! Read through to check out what we know about Reeves's romantic history and whether he's got new love on the horizon or not.
Sandra Bullock
Yes, the Speed costars and famous friends really did have a brief romantic connection in 1993. Both stars recently revealed in separate interviews [5] that they totally had crushes on each other [6] during the movie's filming, but neither knew the other felt the same way! Although they didn't technically date, their friendship has lasted for decades, long past those old crushes.
Sofia Coppola
A movie set led to Reeves's next romance as well. He reportedly met Sofia Coppola while he was shooting Bram Stoker's Dracula with her father, director Francis Ford Coppola. The couple were often spotted together over the next couple of years [7] and broke up around 1992. She went on to marry Spike Jonze, who she divorced in 2003, then Thomas Mars, to whom she's been married since 2011.
Jill Schoelen
Reeves and Schoelen costarred in the 1986 film Babes in Toyland, and they reportedly dated for about three years following their meeting on the set. After their breakup, Schoelen moved on to another actor: Brad Pitt [8]. Schoelen and Pitt were even engaged for three months in 1989 before she broke it off with him as well.
Jennifer Syme
Reeves's most significant relationship was with actress Jennifer Syme, who kept a very low profile throughout their relationship. They began dating in 1998 and, in 1999, Syme became pregnant with their daughter, Ava. Tragically, Syme suffered a stillbirth [9], and their relationship didn't survive long after the loss of their child. The couple did remain friends, though, but any hope of reconciliation was dashed with a second tragedy: Syme died in a car crash in 2000.
Claire Forlani
The pair never quite confirmed their romance, but most sources believe they were dating from about 2004 to 2006 [10]. At one point, there was even a rumour that Reeves had proposed, but at the time, he laughed it off [11] and claimed they were just "good friends."
Winona Ryder
OK, so they never actually dated — but they might be technically married? In 2018, Ryder and Reeves revealed in an interview that a real priest performed the wedding between their characters in Dracula, joking that they might actually be married [12]. While we're pretty sure it wasn't actually legally binding, it's a fun story, especially coupled with their admission of mutual crushes [13] back in the day.
Alexandra Grant
During the LACMA Art + Film Gala in LA on Nov. 2, the actor sparked romance rumours when he was spotted holding hands with artist Alexandra Grant, 46, on the red carpet. Though Keanu hasn't spoken publicly about their current relationship status, the two are longtime friends and collaborators.
Grant previously worked with Reeves on his 2011 book Ode to Happiness and his 2016 book Shadows, and in 2017, the pair founded a publishing house called X Artists' Books [14].